Triethylamine → HCID 58138293, compound

HRID 1260418Notes

Reaction equation

HRID 1260418 reaction equation
[CH2:1]([N:8]([CH3:17])[C:9]1[C:14]([F:15])=[CH:13][NH:12][C:11](=[O:16])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=[O:24].CCN(CC)CC>C(Cl)Cl>[CH2:1]([N:8]([CH3:17])[C:9]1[C:14]([F:15])=[CH:13][N:12]([C:23]([C:19]2[S:18][CH:22]=[CH:21][CH:20]=2)=[O:24])[C:11](=[O:16])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 178482714HCID 178482714, compound

Product 1

HCID 58138293HCID 58138293, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a round-bottomed flask charged with 4-(benzyl(methyl)amino)-5-fluoropyrimidin-2(1H)-one (250 mg, 1.06 mmol) in CH2Cl2 (11 mL) and 2-thiophene carbonyl chloride (172 mg, 1.1 mmol, 1.1 eq) was added Et3N (237 mg, 2.35 mmol) at 0° C. under N2. The reaction mixture was warmed to room temperature after complete addition and stirred at for 12 h. The reaction mixture was diluted with CH2Cl2 (25 mL), washed with satd aq NaCl solution (10 mL), dried over Na2SO4 and evaporated to dryness in vacuo at room temperature. The crude product was purified by reverse phase chromatography to yield the product as a white solid (23 mg, 6%): mp 101.3-102.4° C.; 1H NMR (methanol-d4) δ 8.10 (d, J=6.3 Hz, 1H), 8.00 (d, J=3.8 Hz, 1H), 7.91 (d, J=4.9 Hz, 1H), 7.38-7.20 (m, 6H), 4.88 (s, 2H), 3.22 (d, J=3.2 Hz, 3H); ESIMS m/z 344 ([M+H]+).

Workup

  1. additionafter complete addition
  2. washwashed with satd aq NaCl solution (10 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness in vacuo at room temperature
  5. customThe crude product was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-43e9fd4d360b4151824c5bd2134c1ce0
Source dataset
uspto-grants-2013_06
Patent number
US08470839B2

Reaction notes

Loading…